EP0211030A1 - Ferro-electric smectic liquid crystal materials based on terpenoid derivatives. - Google Patents
Ferro-electric smectic liquid crystal materials based on terpenoid derivatives.Info
- Publication number
- EP0211030A1 EP0211030A1 EP86900815A EP86900815A EP0211030A1 EP 0211030 A1 EP0211030 A1 EP 0211030A1 EP 86900815 A EP86900815 A EP 86900815A EP 86900815 A EP86900815 A EP 86900815A EP 0211030 A1 EP0211030 A1 EP 0211030A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- derivative
- terpenoid
- liquid crystal
- group
- linked
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K19/126—Compounds containing at least one asymmetric carbon atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K19/2021—Compounds containing at least one asymmetric carbon atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K19/2021—Compounds containing at least one asymmetric carbon atom
- C09K19/2028—Compounds containing at least one asymmetric carbon atom containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -COO-CH*-CH3
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/22—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and nitrogen atoms as chain links, e.g. Schiff bases
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/50—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing steroidal liquid crystal compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K2019/3095—Cyclohexane rings in which the end group is the monoterpene menthyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Nouveaux dérivés d'alcools de terpénoïdes cycliques et acycliques ayant la formule (I) X-(CO)n-O-T1, où n = O ou 1, T1 est un groupe de terpénoïdes et X est une combinaison de groupes cycliques, par ex. phényle, cyclohexyle et pyrimidyle. X contient de préférence jusqu'à trois groupes cycliques. Des dérivés préférés sont des esters d'alcools de terpénoïdes cycliques, par ex. menthol, borneol et isopinéocampheol, par ex. formule (II) (-)-menthol. Des mélanges et dispositifs à cristaux liquides smectiques ferroélectriques contenant ces dérivés sous forme de dopants de chiralité dans un hôte smectique renversé sont également décrits. Les propriétés de divers autres dérivés d'alcools de terpénoïdes de formule (I) sont aussi écrites, par ex. celles de néomenthol, isolongifolol, fenchol, carvéol, myrthénol, nopol, citronellol, alcool de perilla et dihydrocitronellol.New alcohol derivatives of cyclic and acyclic terpenoids having the formula (I) X- (CO) n-O-T1, where n = O or 1, T1 is a group of terpenoids and X is a combination of cyclic groups, e.g. phenyl, cyclohexyl and pyrimidyl. X preferably contains up to three cyclic groups. Preferred derivatives are alcohol esters of cyclic terpenoids, e.g. menthol, borneol and isopineocampheol, e.g. formula (II) (-) - menthol. Ferroelectric smectic liquid crystal mixtures and devices containing these derivatives as chirality dopants in an inverted smectic host are also described. The properties of various other terpene alcohol derivatives of formula (I) are also written, e.g. those of neomenthol, isolongifolol, fenchol, carveol, myrthenol, nopol, citronellol, perilla alcohol and dihydrocitronellol.
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB08501999A GB2170214A (en) | 1985-01-26 | 1985-01-26 | Ferroelectric smectic liquid crystal mixture |
GB8501999 | 1985-01-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0211030A1 true EP0211030A1 (en) | 1987-02-25 |
EP0211030B1 EP0211030B1 (en) | 1991-04-03 |
Family
ID=10573460
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86900815A Expired - Lifetime EP0211030B1 (en) | 1985-01-26 | 1986-01-24 | Ferro-electric smectic liquid crystal materials based on terpenoid derivatives |
Country Status (6)
Country | Link |
---|---|
US (1) | US4784793A (en) |
EP (1) | EP0211030B1 (en) |
JP (1) | JPH07585B2 (en) |
CN (1) | CN86101036B (en) |
GB (1) | GB2170214A (en) |
WO (1) | WO1986004328A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PT107134B (en) * | 2013-08-28 | 2015-07-30 | Mfobmx Unipessoal Lda | BICYCLE PEDALURE TIGHTENING AND FASTENING SYSTEM |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3577211D1 (en) * | 1984-06-07 | 1990-05-23 | Seiko Instr Inc | LIQUID CRYSTAL CONNECTION. |
US5236618A (en) * | 1984-07-11 | 1993-08-17 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystal phase |
GB8428653D0 (en) * | 1984-11-13 | 1984-12-19 | Secr Defence | Diesters |
GB8524879D0 (en) * | 1985-10-09 | 1985-11-13 | Secr Defence | N-substituted amino acid derivatives |
WO1987005015A1 (en) * | 1986-02-17 | 1987-08-27 | MERCK Patent Gesellschaft mit beschränkter Haftung | Chiral compounds |
US5180521A (en) * | 1986-02-17 | 1993-01-19 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Chiral compounds |
WO1987005018A2 (en) * | 1986-02-17 | 1987-08-27 | MERCK Patent Gesellschaft mit beschränkter Haftung | Optically active compounds |
EP0268198B1 (en) * | 1986-11-20 | 1993-09-01 | F. Hoffmann-La Roche Ag | Ferroelectric liquid crystals |
EP0269963B1 (en) * | 1986-11-28 | 1995-02-22 | F. Hoffmann-La Roche Ag | Ferroelectric liquid crystals |
GB8629322D0 (en) * | 1986-12-08 | 1987-01-14 | Secr Defence | Cyano-terpenoid esters |
US5232625A (en) * | 1986-12-08 | 1993-08-03 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Cyano-alicyclic esters in liquid crystal compositions |
US4956488A (en) * | 1987-04-13 | 1990-09-11 | Adeka Argus Chemical Co., Ltd. | Optically active cyanobiphenyl compound |
JPH06104827B2 (en) * | 1987-07-31 | 1994-12-21 | キヤノン株式会社 | Ferroelectric liquid crystal element |
JPH0759567B2 (en) * | 1987-07-15 | 1995-06-28 | 旭電化工業株式会社 | Pyrimidine compound |
DE3887048D1 (en) * | 1987-09-19 | 1994-02-24 | Hoechst Ag | Liquid crystalline, in particular ferroelectric, liquid crystalline mixtures. |
JPH01106874A (en) * | 1987-10-21 | 1989-04-24 | Chisso Corp | Optically active phenylpyrimidine compound and liquid crystal composition |
JP2691405B2 (en) * | 1987-11-06 | 1997-12-17 | チッソ株式会社 | Ferroelectric liquid crystal composition |
KR900014300A (en) * | 1989-03-22 | 1990-10-23 | 우메모토 요시마사 | Liquid crystal light modulation device using an optically active compound, a liquid crystal composition containing the compound and a composition |
US5187248A (en) * | 1989-05-26 | 1993-02-16 | Basf Aktiengesellschaft | Monomers and their use for the production of a laser-optical recording element which can be repeatedly erased and recorded on |
US5187298A (en) * | 1990-05-18 | 1993-02-16 | Basf Aktiengesellschaft | Monomers and their use for the production of a laser-optical recording element which can be repeatedly erased and recorded on |
US5212027A (en) * | 1990-05-18 | 1993-05-18 | Basf Aktiengesellschaft | Monomers and their use for the production of a laser-optical recording element which can be repeatedly erased and recorded on |
JPH04218018A (en) * | 1990-06-14 | 1992-08-07 | Hoechst Japan Ltd | Manufacture of liquid crystal cells |
GB2280681B (en) * | 1993-08-06 | 1998-03-11 | Merck Patent Gmbh | Thermochromic media |
US6010643A (en) * | 1994-12-03 | 2000-01-04 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Cholesteric polymer network |
GB2297556B (en) * | 1995-01-31 | 1998-08-26 | Merck Patent Gmbh | Liquid crystalline material comprising terpenoids |
TW585898B (en) * | 2002-12-26 | 2004-05-01 | Ind Tech Res Inst | Liquid crystal compounds with optical activities having high helical twisting power, method for preparing the same, and liquid crystal composition containing the compounds |
JP5217429B2 (en) | 2007-01-18 | 2013-06-19 | Jnc株式会社 | Cholesteric liquid crystal composition |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5692836A (en) * | 1979-12-27 | 1981-07-27 | Seiko Epson Corp | Optically active compound |
JPS5740581A (en) * | 1980-08-25 | 1982-03-06 | Seiko Epson Corp | Liquid crystal composition |
US4514045A (en) * | 1981-06-22 | 1985-04-30 | Minnesota Mining And Manufacturing Company | Helichromic-smectic liquid crystal compositions and display cells |
US4613209A (en) * | 1982-03-23 | 1986-09-23 | At&T Bell Laboratories | Smectic liquid crystals |
DE3377219D1 (en) * | 1982-11-26 | 1988-08-04 | Hitachi Ltd | Smectic liquid crystal compounds and liquid crystal compositions |
EP0115693B1 (en) * | 1983-01-06 | 1987-08-26 | Chisso Corporation | Liquid crystalline compounds and mixtures thereof |
US4614609A (en) * | 1983-06-14 | 1986-09-30 | Chisso Corporation | Liquid crystalline biphenyl derivatives and mixtures thereof |
JPH0726099B2 (en) * | 1984-11-13 | 1995-03-22 | 英国 | Α-Hydroxycarboxylic acid derivatives suitable for liquid crystal materials and devices |
EP0201554B2 (en) * | 1984-11-13 | 1993-01-27 | The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and | Compounds for ferroelectric liquid crystal devices |
US4615586A (en) * | 1985-04-26 | 1986-10-07 | At&T Bell Laboratories | Liquid crystal devices |
-
1985
- 1985-01-26 GB GB08501999A patent/GB2170214A/en not_active Withdrawn
-
1986
- 1986-01-24 WO PCT/GB1986/000046 patent/WO1986004328A1/en active IP Right Grant
- 1986-01-24 US US06/913,671 patent/US4784793A/en not_active Expired - Lifetime
- 1986-01-24 CN CN198686101036A patent/CN86101036B/en not_active Expired
- 1986-01-24 EP EP86900815A patent/EP0211030B1/en not_active Expired - Lifetime
- 1986-01-24 JP JP61500852A patent/JPH07585B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
See references of WO8604328A1 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PT107134B (en) * | 2013-08-28 | 2015-07-30 | Mfobmx Unipessoal Lda | BICYCLE PEDALURE TIGHTENING AND FASTENING SYSTEM |
Also Published As
Publication number | Publication date |
---|---|
CN86101036B (en) | 1987-04-22 |
GB2170214A (en) | 1986-07-30 |
JPH07585B2 (en) | 1995-01-11 |
JPS62501559A (en) | 1987-06-25 |
EP0211030B1 (en) | 1991-04-03 |
CN86101036A (en) | 1986-12-03 |
US4784793A (en) | 1988-11-15 |
WO1986004328A1 (en) | 1986-07-31 |
GB8501999D0 (en) | 1985-02-27 |
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